Continued changes to healthcare delivery in the UK, and an increasing focus on patient safety and quality improvement, require a radical rethink on how we enable graduates to begin work in challenging, complex environments. Professional regulatory bodies now require undergraduate medical schools to implement an "assistantship" period in the final year of study, where senior medical students "shadow" the work of junior doctors, with an expectation that they will be better "prepared" for work. However, there is little guidance about what an "assistantship" entails and the current emphasis on preparedness of students arguably underplays the importance of contextualised learning within the workplace environment. This paper will describe a modified Development Work Research (DWR) (Engeström in Developmental work research: activity theory in practice. Lehmanns Media, Berlin, 2005) approach to organisational change, enabling academic, clinical and administrative partners to develop assistantship placements in different hospitals. Our findings indicate that a modified DWR approach can reveal factors indicating organisational readiness to support change within a locally contextualised framework. The process has significant practical applications across a range of healthcare disciplines, as all professions seek to engage with the challenge of enabling successful transitions of graduates to the workplace.